Potassium Carbonate → 2-(4-Amino-3-methylphenoxy)-5-fluorobenzonitrile

HRID 220216

Reaktionsgleichung

Reaktionsgleichung von HRID 220216
F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=2[C:4]#[N:5])=[CH:14][C:13]=1[CH3:19]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 178194-Amino-m-cresolHCID 1235582,5-Difluorobenzonitrile

Produkt 1

HCID 574187552-(4-Amino-3-methylphenoxy)-5-fluorobenzonitrileAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

In a 5 L flask that had been evacuated and back-filled with Argon, 2,5-difluorobenzonitrile (1092 mL, 3057 mmol) and 4-amino-3-methylphenol (376.5 g, 3057 mmol) were dissolved in dry DMSO (2.75 M) with rapid stirring at ambient temperature. The solution was evacuated/backfilled with Argon. Potassium carbonate (697.2 g, 5044 mmol) was added. The reaction was evacuated/backfilled with Argon and warmed to 81° C. for 14 hours. After cooling to ambient temperature, the reaction was poured slowly into 3 separate beakers, each containing 2.5 L of rapidly stirring ice water to prevent clumping. The residue in the round bottom flask was taken up in water repeatedly and poured into the beakers until a total volume of 3.5 L was realized in each of the three beakers. The suspension was stirred rapidly for 2 hours as it came to ambient temperature. The brown solids were collected by filtration, washed with water (15 L), air dried, dried with latex dam, and dried under high vacuum at 45° C. for 72 hours to provide 734 g (99%) of desired product as a tan solid. MS M+1 (243).

Aufarbeitung

  1. customIn a 5 L flask that had been evacuated
  2. temperaturewarmed to 81° C. for 14 hours
  3. temperatureAfter cooling to ambient temperature
  4. additionthe reaction was poured slowly into 3
  5. customseparate beakers
  6. additionpoured into the beakers until a total volume of 3.5 L
  7. stirringThe suspension was stirred rapidly for 2 hours as it
  8. customcame to ambient temperature
  9. filtrationThe brown solids were collected by filtration
  10. washwashed with water (15 L), air
  11. customdried
  12. customdried with latex dam
  13. customdried under high vacuum at 45° C. for 72 hours

Quellen und Nachweise

ORD-Eintrag
ord-c820980958d745c4804729e487e542ed
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202899B2

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